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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
This episode features a fascinating discussion between Harry Stebbings, Jason Lemkin, and Rory O'Driscoll about the current state of venture capital, AI valuations, and the shifting landscape of B2B software. The trio dissects an Iconic report revealing that AI-native companies achieve better burn multiples despite lower margins due to their explosive growth rates. (04:12) They explore the challenges facing traditional B2B companies in securing funding, the massive energy requirements of AI infrastructure, and significant M&A activity including EA's record-breaking $55 billion take-private deal.
Host of 20VC, one of the world's largest venture capital podcasts. Harry has built a media empire around venture capital content and maintains one of the most influential voices in the startup ecosystem.
Founder and Managing Director of SaaStr, having previously founded EchoSign which was acquired by Adobe for $200 million. Jason is a prolific writer and speaker on SaaS business models and venture capital trends.
Investment partner at Scale Venture Partners, where he focuses on B2B software investments. Rory brings decades of venture capital experience and has been involved in numerous successful enterprise software deals.
The speakers emphasize that even companies with strong metrics should prioritize securing funding over optimizing valuation. Jason warns against "toxic" advice from VCs still operating with 2021-2022 mentality. (18:00) Even companies achieving triple-triple-double-double growth rates are struggling to raise capital if they're not clearly AI-native. The advice is stark: if you receive a reasonable offer, take it immediately rather than trying to optimize terms.
According to the Iconic report discussed, AI-native companies show -126% free cash flow margins compared to -56% for traditional software companies. However, their burn multiples are actually better because they're growing so rapidly. (05:15) This means they generate more ARR per dollar spent, making them more attractive to VCs despite seemingly worse unit economics.
The speakers discuss how being a clear market leader in AI segments provides unprecedented advantages. (23:00) Buyers are under pressure to make AI purchases but don't know who to trust, making brand recognition and market position incredibly valuable. This creates a "kingmaker" effect where leading companies deter investment in competitors simply through their market presence.
With 600-700 unicorns and only 15 IPOs year-to-date, VCs must combine portfolio companies to create IPO-worthy entities. (54:29) The Fivetran-DBT deal exemplifies this trend, where combining complementary companies makes strategic sense despite ownership dilution. VCs are learning that 8% of something that can go public is better than 20% of something that can't.
The traditional model of B2B software remaining static for years is dead. (62:31) Jason points out that products like Pipedrive didn't change for four years, but today's AI-driven market demands constant innovation. Companies can't wait years to launch new features, making private equity's traditional "buy and optimize" model much riskier.